Where Entrepreneurs Come to Win
Premium business coaching, strategy, and media for entrepreneurs ready to build profitable,
purpose driven companies — led by Jay Adewole, Harvard alumni, two-time award winner, and multi-million-dollar sought-after business coach.
Clarity. Structure. Confidence. Growth.
The four pillars of The Winners Circle.
More Than a Podcast — It’s a Global Entrepreneurial Ecosystem.
The Winners Circle connects business strategy, media, education, and leadership development into one powerful platform. Whether you're a new entrepreneur or a growing CEO, this is where clarity, structure, and success begin.
The Winners Circle Podcast
Deep, thought-provoking conversations with entrepreneurs, creators, executives, and global leaders.
Business Coaching
Premium monthly 1:1 coaching and strategic support for entrepreneurs and leaders ready to scale with confidence.
Winners Circle Webinar
Live business training led by Jay — focused on strategy, leadership, and high-performance execution.
The Winners Circle Business Transformation Program
A premium 8–12 week strategic coaching and implementation experience designed for service-based entrepreneurs, consultants, and founders ready to scale beyond hustle.
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Everything You Need to Win
Explore the full Winners Circle ecosystem — a powerful suite of coaching, content, resources, and strategic tools created to help entrepreneurs build profitable, purpose-driven businesses with clarity, confidence, and precision.
Business Coaching
For entrepreneurs and leaders who are ready to elevate their strategy, strengthen their structure, and operate with clarity.
Jay’s coaching programs are designed to help you scale with confidence and build a business aligned with long-term growth and impact.
Events & Webinars
Attend exclusive masterclasses, live trainings, and virtual workshops hosted by Jay Adewole.
Each session is designed to elevate your business strategy and prepare you for the next level in your entrepreneurial journey.
The Winners Circle Podcast
Go behind the scenes with real conversations from top entrepreneurs, executives, creators, and industry leaders.
Gain insight, wisdom, and strategies that challenge your mindset and expand your capacity for growth.
Books by Jay Adewole
Explore powerful business frameworks, growth principles, and success strategies written by Jay.
These books offer practical, actionable lessons you can apply directly to your life and business.
Winners Spotlight Magazine
A premium business publication featuring high-performing entrepreneurs, CEOs, and innovators.
Learn from their journeys, discover powerful insights, and connect with leaders shaping the future of business.
Winners Circle Business Transformation Program
A premium 8–12 week strategic coaching and implementation experience designed for service-based entrepreneurs, consultants, and founders ready to scale beyond hustle.
The program helps you clarify your business model, elevate your offer and pricing, install scalable systems, and step fully into the CEO role—so you can grow a structured, profitable business positioned for $15K–$50K+ months with clarity and control.
Meet Jay Adewole
Jay Adewole is a two-time award-winning, Harvard alumni, multi-million-dollar sought-after business coach, and Managing Partner at Point of View Consulting in New York.
He is the host of The Winners Circle Podcast and founder of Winners Spotlight Magazine, helping entrepreneurs and leaders build profitable, purpose-driven businesses.
Through coaching, strategy, and leadership development, Jay helps businesses move from confusion to clarity, from scattered to structured, and from potential to real power.
“The Winners Circle” was created as a space for entrepreneurs who refuse to settle — leaders who want to win in business without losing their values, family or identity.
THE WINNERS CIRCLE BUSINESS COACHING
Monthly Coaching Plans with Jay Adewole
Premium guidance for entrepreneurs who want clarity, structure, and scalable growth.
Listen to The Winners Circle Podcast
Conversations that challenge you, inspire growth, and elevate your thinking.
The Future of Work: Embracing AI Agents as Valuable Team Members
Transforming Life through the Power of Self-Awareness with Evan Marks
Avoiding Burnout as an Overwhelmed Entrepreneur
"My life changed forever"
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Upcoming Webinar: How to Build & Scale Your Business in 2026
Join Jay live on December 17th for a powerful session on strategy, systems, pricing, leadership, and growth.
All attendees will receive the Winners Circle 2026 Business Growth Toolkit, including:
What You’ll Learn:
How to build a strategy that actually works
The 3 systems every entrepreneur needs
How to create high-ticket offers
How to attract premium clients
How to scale without stress or confusion
BONUS INCLUDED:
Every attendee receives the Winners Circle 2026 Business Growth Toolkit, featuring:
2026 Strategic Plan Template
Pricing Reset Worksheet
Operations & Systems Checklist
CEO Leadership Habits Guide
What Entrepreneurs Are Saying
TESTIMONIAL 1
TESTIMONIAL 2
TESTIMONIAL 3
TESTIMONIAL 1
TESTIMONIAL 2
TESTIMONIAL 3
"My life changed forever"
"Highly recommend this"
"Highly recommend this"
JOIN THE WINNERS CIRCLE COMMUNITY
Be the First to Receive Exclusive Tools, Events & Resources
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